


If You're Going To Hell, You May As Well Run

by writethelifeyouwant



Category: Supernatural
Genre: Bondage, Dirty Talk, Drinking, F/M, Last Day On Earth, M/M, Multi, No Wincest, Smut, Threesome - F/M/M, Truth or Dare, rough
Language: English
Status: Completed
Published: 2019-07-23
Updated: 2019-07-25
Packaged: 2020-07-12 11:20:27
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 7,084
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19945321
Author URL: https://archiveofourown.org/users/writethelifeyouwant/pseuds/writethelifeyouwant
Summary: You had a spell placed on you as a tiny child determining your time of death. Sam and Dean have tried to find a way of breaking it but they have not found a way to help. You accepted your fate already, and you just want to enjoy the time you have left.





	1. Chapter 1

**Author's Note:**

> So this is the first time I have written anything remotely like this. Of course I would dive into the deep end of like the kinkiest smut ever my first around because why go easy on yourself. I hope this goes down well.

“There’s gotta be something else we can do.” 

“Well I’m trying here Sam but I’m coming up with bupkis.” Dean shoved himself back from the table in frustration and throwing up his hands. 

“Guys we have tried everything, we have read every bit of lore in this bunker, there’s nothing we can do. It’s time to stop.” Y/N said. 

“We aren’t just gonna sit here and wait for you to expire Y/N,” Sam huffed. 

“Sam we have been over this, it’s fine. I was fine with it before, I’m fine with it now. I knew this was coming.” 

“Y/N come on you can’t mean that,” Dean said. “No one wants to die.” 

“Of course I don’t want to, Dean,” you sighed. “But I also don’t want to spend my last night on earth googling obscure astrological references and trying to beat fate.” 

“Well what else do you suggest we do?” Dean huffed. You crack a smile as you cross the room to a cherry cabinet, pulling out two mostly full bottles of scotch. 

“Drink.” Pulling the stop out of one of the bottles you grab an old fashioned glass and fill it nearly to the brim before you take a large swig. Dean and Sam just stare at you with pained but slightly bemused expressions. “You guys joining me?” 

-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*

“Absolutely not,” Dean shuts you down. “We are not a bunch of douche-wad tweens. We are not playing truth or dare.” 

“Oh come on,” you say, dragging out the last word as you reach across the table to grab his fist. “I’m dying you have to do what I want,” you pout, your eyes pleading. 

“She has a point Dean,” Sam admits, taking a deep drink of his scotch. 

“Alright fine,” Dean downs the last of his drink and reaches to pour another. “But pull up one of those game apps or something on your phone. I’m not gonna sit here doing some lame ass dares because Sam can’t think of anything good.” 

“Fine,” you stick your tongue out at him as you pull out your phone and try to download something. After a moment you have a new app loaded and you place your phone in the center of the table. “Who’s going first?” 

“I think that’s gonna be you, princess,” Dean spun the phone towards you. 

“Okay!” You drew a digital card from the pile and a dare came up. In big scary red letters the dare flashed on the screen. REMOVE ONE ITEM OF CLOTHING. “Shit,” you grumble to yourself. You were only wearing a t-shirt and shorts. 

“Ha, sucks for you,” Dean smirked and sipped at his drink. “You picked the game sweetheart.” 

“Yeah, yeah, shut up.” You proceed to pop open the button on your denim shorts and shimmy out of them, thanking god you were wearing underwear that actually provided some coverage. “Your go Sam,” you push the phone towards him and he reaches out to draw from the digital deck. 

TRUTH flashes up on the screen before giving way to the question. “How was your first kiss?” Sam reads aloud. He sits back in his chair, considering for a moment before he answers, “Really awkward. Your turn Dean,” he slid the phone towards his brother but you interrupt before Dean has a chance to draw. 

“Woah woah woah, you’ve gotta give up more than that! I had to take my shorts off!” You protest. 

“Fine,” Sam elaborates. “I was eleven, the girl’s name was Chrissy Mills and after we kissed she never spoke to me again.” Dean snickered behind his drink. 

“Oh my god why? Was it that bad?” 

“Well, I tried to shove my tongue down her throat because my idiot brother told me that’s what you’re supposed to do.” Sam glared over at Dean and this time he couldn’t conceal his amusement. 

“Hey, I was just giving you helpful hints Sammy. Not my fault you tripped up on the execution.” 

“Yeah whatever, your turn jerk.” 

Dean reached for the phone and drew a card. TWERK FOR THIRTY SECONDS. “What is a twerk?” 

-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*-*

You were nearing the bottom of the second bottle of whiskey, which wasn’t as bad as it sounded considering your drinking partners were essentially functioning alcoholics but still, you were all feeling it. As you leant forward on the table to rest your head on your hand you noticed how soft your cheek felt. Completely distracted, you continue to run your fingers up and down your face, trying to decide whether it felt more like velour or velvet. 

“Hey,” Sam snapped his fingers in front of your face, jolting your focus back to your companions. “Earth to Y/N, we losing you?” 

“No, nope, we’re good. So good,” you give two ‘okay’ signs with your fingers. 

“You wanna tap out?” Dean asks. 

“No,” you shake your head again to clear it. “It’s your turn Dean, come on.” 

“Okay, what’ve we got.” Dean rubbed his hands together in anticipation. Smirking, he decides to read the dare aloud, “Keep your hand on the very inner thigh of the person next to you for the next round.” Dean flicked his eyes between you and Sam. 

“Don’t look at me, dude.” Sam took a swig of his drink to cover his his mouth as a smug grin pulled at the corners of his lips. It had been clear over the past few days how attractive you found both the brothers and Sam knew what this was about to do to you. 

“Okay, get over here sweetheart.” Dean was grinning like a madman, wiggling his eyebrows for comedic effect. He slid his chair closer to yours and you felt hot fingers brush teasingly against your knee. Your whole body flushed almost instantly, and you were suddenly very aware of the fact that you had discarded your shorts earlier. Dean’s hand crept further up your leg to wrap firmly around your thigh, and he gave a small pinch far too close to your panties. The squeak you emitted made Sam and Dean break into a series of somehow manly drunk giggles. 

Sam pulls the phone towards himself and draws your card for you. “Okay, Y/N, who is your crush.” You groan, internally panicking. Dying tomorrow or not you weren’t about to tell the brothers what had been playing on your mind since you met them. Grasping for straws in your brain you blurt out the first name you can think of. 

“Um… Robert Downey Jr.”

“Seriously?” Sam laughed. “The guy’s old enough to be your father.” 

“Maybe that’s why I like him,” you shoot back before your brain has a chance to consider whether that was wise. Sam and Dean’s eyes bulged for a moment before they break into teasing grins. You groan internally as you realise that you essentially just admitted to them that you have a daddy kink. Surprisingly, they let it pass without further comment and Sam moved quickly to draw his card. When he pulled it from the pile he groaned as it flashed up on the screen. WHAT’S YOUR BIGGEST KINK? 

“I am not answering that,” Sam stated resolutely as he drained the rest of his glass and poured another. 

“Oh come on, you have to, those are the rules!” you protest. 

“Yeah, Sammy, those are the rules,” Dean backed you up, nodding seriously. 

“Nope,” Sam continued to refuse and took another large gulp of whiskey. 

“I’ll tell you mine if you tell me yours,” you offer, batting your eyelashes at him and flashing a coy smile over the rim of your glass. 

“Okay, now you really have to man,” Dean says eagerly. 

“It’s gonna sound so bad,” Sam stalls, really not wanting to share. You and Dean continue to heckle him until he breaks. 

“Fine, fine I…” Sam takes a deep breath before he can spit out the rest. “I like to tie girls up, okay? Happy?” You and Dean look at each other and burst out laughing. Sam sits back in his chair, extremely put out. “Okay, laugh it up. I’m a freak I get it.” 

“No, Sam, that’s not why I’m laughing! That’s like totally not embarrassing. The way you were acting I thought it was gonna be something really creepy.” 

“Oh yeah, well then what’s yours?” Sam shoots back at you. 

“I’m not telling! Mine’s actually embarrassing, yours was so not worth it.” 

“Aw come on, you promised,” Dean pestered, rubbing his hand further and further up your thigh. 

“I lied,” you said simply, taking another sip of whiskey, trying not to let on to Dean just how much his movements were affecting you. “Your turn,” you spin the phone towards Dean. He draws. CHUG YOUR DRINK.

“Okay then,” He smiles and quickly drains his glass. “You’re up sweetheart.” 

It occurs to you that the round is over and Dean technically doesn’t have to keep his hand on your thigh anymore but he seems to have forgotten, and you don’t remind him. Your card flashes up on the screen, and if you weren’t completely hot and bothered before, you were now. WHAT WERE YOU THINKING ABOUT THE LAST TIME YOU FLEW SOLO? 

Oh dear God, you thought. “Yeah… I’m gonna skip that one.” 

“Oh no you don’t,” Sam grabbed for the phone before you could change the card. “You wouldn’t let me skip! Spill it.” 

Sitting there, Dean’s hand still on your inner thigh, and the images resulting from Sam’s confession about wanting to tie people up playing through your mind, you consider your options. You could make something up. Make it sufficiently embarrassing so the brothers wouldn’t question too much why you wanted to skip the card or… You could tell the truth. 

You knew it was weird and kinky and taboo but you know what, you’re drunk. Really very drunk and it occurs to you, so are Sam and Dean. Steeling your resolve you take a very deep breath and lock eyes with Sam. “You,” you say simply. Sam nearly chokes on his drink. 

“And you,” you add, looking to your side at Dean, whose eyes are blown wide. Figuring you may as well go in for the kill you take another breath and pour your confession into the silence, “at the same time.” 

This time Dean chokes on his drink, pulling his hand away from your thigh to cover his mouth as he coughs. You stare into your lap, face bright red, not sure yet if you should be regretting your admission. Dean finds his voice a second later. 

“You mean,” he splutters, “us,” he points between himself and Sam, “and you,” he points back at you, “all together?” Dean spun his finger in circles in the air, confirming that you were, in fact, talking about having a threesome with him and his brother. Your face and body burned hotter than the whiskey going down your throat had ever made you feel. You were beyond embarrassed that you just admitted out loud to one of your deepest fantasies but part of the warmth now coursing through your veins was directly correlated to the look of lust that had darkened Sam’s eyes as he absorbed this new information. 

The mortification winning out, you abruptly push back your chair, startling both brothers out of their statuesque reveries. You try to hurry around the table but you’re on the side farthest from the hallway that could lead to your escape. Trying to make your exit you rush past them but are stopped by a stone grip on your wrist.


	2. Chapter 2

“Y/N…” Sam’s call is low and measured and its confident tone settled a dense weight across your lungs as your breath caught audibly in the silence of the room. The scratching of chair legs on the floor scraped against your ears and Sam moved behind you. He let go of your wrist and rested his hands solidly on the sides of your shoulders, keeping you anchored to him as he leant forward and pressed a kiss to the top of your head. It was easy to do, he towered over you. 

The feel of his hands on the bare skin of your arms and his nose pressed into your hair was electrifying. Your heart was pounding so loudly in your own ears you missed the sounds of Dean getting up from his chair to move towards the frozen pair that you and Sam had become. 

Your eyelids had sighed closed but they fluttered open at the feel of fingertips dragging lightly over the peach fuzz of your jaw. You recalled how barely a few minutes ago you had done the same thing to yourself, ghosting your knuckles over your face and admiring how plush the alcohol had made your skin feel. Having Dean’s hands on your face was ten million times better. 

The green of his eyes had become incandescent, his bewildered expression of a few moments ago replaced by a steady confidence and burning excitement. His eyes held yours captive as he pushed carefully closer, encircling your face in his grasp before he leaned in, his breath the barest rasp against your lips. Your own breath stuttered out as you realised you had neglected to breathe since Sam had pressed his lips to your head. A hint of a smile played across Dean’s face before he closed the empty millimeters separating your lips from his. The rough, dry skin of his mouth skimmed over yours, teasing your senses into overt anticipation. 

He pulled back and dragged his hands down along your neck and brought them to settle gently over Sam’s hands, still grasping your shoulders, essentially keeping your body from bursting out of its skin. Dean’s hands squeezed Sam’s further into your flesh, and they exchanged a look over your head, solidifying their decision wordlessly as they had done so often before. Slowly, Sam and Dean released you. Sam stepped to your side and grabbed one of your hands, anchoring his other firmly on your lower back while he began to move you forwards. Dean grabbed your other hand, using it to pull you down the hall as he walked backwards with heavy, deliberate steps. His gaze drew you towards him, and Sam’s hands guided you into Dean’s room and pressed you into Dean’s body, keeping you imprisoned there with his own frame. 

Sam bent and gently pressed his soft, wet lips to the shell of you ear, then dragged them down to the skin of your neck, leaving a glowing trail in his wake. Dean moved to the other side, his rougher lips grazing your skin, hovering and scraping over it, not giving you the pressure and the satisfaction your skin was burning for. The next second your composure shattered and you spun, throwing yourself against Sam and taking the kiss you so desperately craved. You wrapped your arms around his neck so you could hold yourself against him and keep your faces level as his kiss took you over completely. 

Sam’s hands shoved themselves into your hair as his lips and tongue moved against yours, tugging and pulling you to where he wanted. Your tongues slid together breathlessly, your hands clutched at each other, your lips melted together, moulding and remoulding over and over again. You moaned when you felt Dean move behind you, pushing your hair aside so he could kiss along the back or your neck. His lips burned into you as his hands trailed harshly down your sides and circled themselves tightly around your waist. 

You were enveloped in them. Their bodies were the only thing that mattered. It didn’t matter that you were all tired, that you were all completely drunk, that for you, the world was about to be snuffed out. You didn’t care. Sam and Dean were the only thing you wanted to think about for the rest of your life. 

Deciding it was time he got a turn, Dean tugged roughly on your arms, pulling them off of Sam and guiding them back over your shoulders to find a new grip clasped around the back of his head. You fell off of Sam and rolled your head to the side, kissing Dean wetly over your shoulder, using his hair to pull him closer against you. Dean’s hands slid down your arms and over your chest, holding one breast in each hand as he crushed you to him. Sam watched you both, breathing heavily as he took a moment to compose himself and decided what he wanted to do with you next. 

You groaned as Dean pulled his lips away from yours. He pushed your head to the side so he could kiss along your neck and your head slumped back onto his shoulder as you opened yourself to his touch. His lips were forceful now where they had been teasing before. He licked and sucked over the sensitive skin under his mouth while he massaged you through your bra, dragging the lace of it over your skin deliciously. Flickering your eyes open you looked forward and gasped as you saw Sam unbuttoning his plaid and letting it fall to the cement floor. He pulled his t-shirt over his head and it left his hair tousled in the sexiest way you had ever seen. 

Noticing how Sam was staring at your hands, still gripped behind his own head, Dean smiled and pulled his lips off of you with a wet, sucking sound. “Sammy, why don’t you grab that rope I have in my bag,” he panted, grinning when he saw Sam’s eyes light up in response. You shuddered as you realised what Dean was suggesting. You barely had more than a moment before you felt Sam’s calloused hands grabbing your wrists and pulling them together behind Dean’s neck, stretching your muscles deliciously. The rough brush of rope fibers made itself known against your skin but it was just a tempting touch, like Sam was only teasing you with the idea. 

“Y/N,” Sam’s voices croaks out your name as a question, raspy from lack of use over the past few minutes. Your mind is racing, so turned on by the thought of being bound and at the mercy of these two men you can barely get out the words to let them know this is okay. 

“Yes,” you finally manage to breathe, your voice twitching like a leaf on the wind. Dean growls his approbation against your skin, where he’s gone back to pressing hot wet kisses onto your neck and behind your ear. Sam says nothing at all, but immediately loops the rope around your wrists, tying them securely together. The feel of the binding is more arousing than you could have believed. You had always wanted to try this, to explore the side of you that you knew wanted to be taken and used by someone however they wanted; the side of you that wanted to float into the blissful feeling of accepting how helpless you really were; to surrender. 

Sam pushed your bound wrists back over Dean’s head, releasing some of the strain on your shoulders. You turned breathlessly to face them, eyes shining with desire and desperate hope. Sam smirked, eyes trained on the knots keeping your wrists bound. His chest was visibly heaving with excitement and knowing that looking at you was what was making him feel like that was exhilarating. 

Grabbing the dangling end of the rope that was trailing from your wrists, Sam used it to pull you over towards Dean’s bed. It was almost humiliating, being dragged along like some sort of prisoner, but that feeling came edged with an intense arousal that seemed to cut across your chest in burning arcs. Sam noticed a small flaw in his plan at this point. Dean’s headboard was solid wood, it didn’t even have end-posts to tie anything to. Deciding to circle back to that problem later he sunk onto the edge of the bed and pulled you to him. You draped your arms over his head and came to rest your forearms on his shoulders. 

Settling yourself over Sam’s hips you lean in to kiss him again. Through the thin layer of your panties you can feel the coarse texture of his jeans spread tightly over the hard body they were concealing. Sam’s hands came to settle on your hips, pushing you down onto him in a forceful rhythm. The friction Sam was creating between your legs felt incredible and your weren’t sure if you preferred the feeling of that, or the feeling of his tongue in your mouth. 

While watching you two Dean had stripped his shirts off and tossed them aside. Coming up behind you he knelt at the foot of the bed and ducked his head under your loose t-shirt. Dean sucked hot, wet kisses into the skin of your back, peppering the canvas with dark little halos. Pushing his hands around the front of you again he dug his fingers into the cups of your bra, pinching at your nipples until he pulled pathetic little whimpers from your mouth. 

Sam pulled back and grinned down at you, admiring the writhing mess he and Dean had already managed to create. You heard a small metallic click come from behind you, and your lust clouded brain doesn’t have a chance to guess at what it could be before you feel something hard and cold press against your collar. Dean drags his knife under the collar of your shirt and pulls hard towards your shoulder. He rips the cotton and the strap of your bra clean in two with one powerful stroke. Repeating the motion on the other side with a satisfied grin, the two unconnected pieces of your shirt fall down your skin, leaving it bunched at your waist. Grabbing at the clasp of your bra Sam flicks in open easily and throws it aside, relishing in his new view. 

“Stand up, princess,” Dean growls and pulls you backwards off of Sam into his body. His chest is hot, and the feel of his bare skin pressed along the length of your bare back is intoxicating. You press yourself into him harder, reaching for one of his hands and pulling it along your stomach up to your breasts. You sigh with relief as he begins to knead your flesh in his hand, using his other to push the t-shirt down over your hips so you are left standing in nothing but your panties. 

“So, what should we do with her Sammy?” Dean asks the questions so coldly, so casually, he could have been talking about anything. You could have been one of the monsters they hunted and imprisoned on a regular basis, and now they were just debating the best way to kill you. Honestly, you weren’t so sure that having a threesome with Sam and Dean wouldn’t kill you anyways, even if that wasn’t their intention. 

“I don’t know Dean,” Sam mused, running his fingers roughly through his hair. “You’ve already been so kind as to indulge me,” he nods at the rope knotted around you, “maybe we should make Y/N tell us what else she wants.” Sam got up from the bed and strode forwards, grabbing your wrists as he reached you and bringing your hands to the bulge in his jeans. Nervously, you begin to stroke him, your motions a bit awkward because of your hands being tied together. 

Dean’s hands trail down your body again and this time dip between your legs. Incredibly lightly, he brushes one fingertip over your clit, smiling at the gasp you let out in response. 

“What was it you didn’t want to tell us earlier, sweetheart?” Dean’s breath rasped across your ear. “Was this your kink? Being with both of us? Letting us have our way with you?” 

Cheeks burning, you shake your head. Of course this was something you had thought about, being with two guys at once. And yeah, you’d thought about being tied up too, but those weren’t your biggest kinks. Those weren’t the ones that embarrassed you. 

“No?” Sam’s brow shot up quizzically. 

“You have something dirtier than this you still don’t want to tell us?” Dean laughed, his finger now drawing teasing circles around the outside of your entrance. 

“Was it the knife?” Sam questioned, his tone was seductive but mixed with a genuine curiosity that you thought only Sam could ever have a chance of pulling off. “I saw your eyes when Dean cut that shirt off.” Sam’s hands had replaced Dean’s on your chest, and his fingers were pulling teasingly at your nipples. Shaking your head, you try to get a grip on yourself and find your voice. 

“No,” you breathe. “I mean, the knife was fine,” your eyes flicked up to meet Sam’s where they seem to be trying to bore a hole through your skull. “But that, that’s not it,” you stutter. 

“You can tell us,” Sam reassures you, stepping closer and cradling your face in his hands. He bends down and pulls you into a searing kiss, sucking all the breath from your body. Dean spins you around and pulls you into a kiss of his own, pulling your tongue inside his mouth and making you dizzy. Pulling back to allow you to catch your breath, Dean’s hazy green eyes burn into yours. 

“We just want to make you feel good baby girl,” Dean croons, and you can feel yourself melting backwards into Sam’s arms, his words shooting flames through your veins. 

“Oh, I think that did something Dean,” Sam chuckled darkly somewhere above you. “You like him calling you baby girl?” Sam breathed the question against the skin of your neck before suckling his own marks along your collar. You whimper and nod, tilting your head to give Sam more room while keeping your eyes locked with Dean’s. “Well that can’t be all it is,” Sam reasons out loud. “That’s hardly taboo considering what else is going on here.” 

Screwing up your courage, you take a deep breath and shut your eyes, allowing yourself to focus on the places Sam and Dean were touching you. You could never say this while you were looking at them, despite, as Sam had pointed out, the fairly taboo nature of what you were already doing. “It’s the names,” you admitted. You brought your hands up to where Sam’s head was still pressed against your neck and buried your fingers in his hair in an attempt to ground yourself. 

“I like being called names.” When you opened your eyes Dean’s grin was hungry. “I like being dominated. I want to be a good girl for you. I want to be yours.” 

“Oh believe me sweetheart,” Dean closed in and caught your face between his hands, “You. Are. Ours.” 

Sam and Dean’s hands shoved you to your knees, and Dean quickly unbuckled his jeans and shoved them and his boxers out of the way. You had imagined this so much since you’d first seen him; Dean’s cock jutting out from his body so close to your mouth. You glance up at him, dark eyes asking for permission. Dean’s only answer was a knowing smirk, and you surged forward to finally taste him in your mouth. 

The feeling was intoxicating. You bring your bound hands up to grasp the base of his cock and you suck the broad head closer and closer to your throat. Dean hummed happily and threaded his fingers through your hair. They met with Sam’s and the brothers’ grasped hands in a brief moment of communication. Sam pulls your head off Dean’s cock suddenly and yanks your arms over your head, pulling you back into himself. 

You can feel Sam’s cock, which must be as large as Dean’s at least, pressing against the back of your head through his jeans. The hand that isn’t holding your arms hostage drops to your jaw and pushes your mouth wide open. 

“Look at her Dean,” Sam hisses. “Look how much she wants this.” You are gasping, so overwhelmed by how much you need this, need Dean’s cock back in your mouth. 

“Yeah, someone’s a little needy, huh baby girl?” 

You mewl. 

“What’s that sweetheart?” Dean cups a hand to his ear, mockingly. 

“Please, Dean.” 

“What do you want?” Sam hisses. “Tell us.” 

“I want you in my mouth Dean, please,” you struggle against Sam’s grip helplessly, trying to close the space between you and Dean. 

“Do you?” Dean asks. “And what does that make you, sweetheart?” 

You’re so overwhelmed, you don’t quite understand what he’s looking for but Sam beats you to an answer. 

“Does that make you our whore?” Sam’s words burned hot through your core, igniting a brutal excitement in your heart. Every molecule of your body was singing with heat and desperation. 

“Yes,” you gasp. “I’m yours, I’m your whore, please-” you whimper.

“Sammy, hold her still.” Dean grips his cock and finally comes closer. He brushes the tip of his cock against your lips, painting them lightly with his precum. “You gonna be a good little slut and let me fuck your mouth?” 

“Yes, please Dean, please.” 

All at once your mouth is full of Dean’s dick and you are nearly choking on its whole length. He eases out for a moment and lets you catch your breath before he feeds himself back in, and you feel him press down your throat. Sam’s hands drag down your neck and press, ever so gently, against the place where Dean’s cock was distending your throat. Dean builds up a steady rhythm, pushing relentlessly in and out of your mouth, balls slapping against your chin, and making an absurd squelching noise that you should not find as arousing as you do. 

“That’s it baby,” Sam praised, brushing the sides of your face and you neck. “You’re taking him so well, letting him fuck you so good.” You moaned around Dean’s cock in your throat and his hips stutter. 

“Sam, it’s your turn man,” Dean grunted. “How do you want our little cockslut?” 

“Bed,” Sam huffed out. “Now.” He pulls you off of Dean and yanks on your arms, almost dragging you back to the bed with him. Dean shed the remainder of his clothes and followed. Sam was unbuckling his jeans now, shoving his boxers down and off with them. Sam is huge. Your eyes balk when you see him without all his layers, his cock bobbing out in front of him, leaking for you. You kneel up on the bed and grab for him. He pulled your head down onto his dick and you sucked hungrily, relishing in his groans of pleasure. 

“That’s it sweetheart,” Dean encouraged, petting his hand down your back. His fingers scorched a path across your spine, then further down, ghosting themselves between your legs. “Woah,” Dean laughs, shooting sparkling eyes up at Sam, “these panties feel like they took a deep dive into a swimming pool. This all for us darling?” You moan the affirmative, sending some very pleasant vibrations up through Sam’s cock. 

He grabbed your hair and started fucking your mouth just as Dean pushed your panties aside and eased one long finger inside you. “Oh Sammy, you should get a load of the view from back here,” Dean grinned, pushing a second finger in alongside his first. He loved watching his fingers disappear inside of you, feeling your body clenched around his, needy and soaking. 

You wrenched your mouth off of Sam, swallowing as much air as you can. “Oh God,” you moan, laying your head down onto your forearms and arching back into Dean’s hand. 

“Greedy little girl, aren’t you?” Sam laughed, pulling on your chin until your face is level with his, and then he’s kissing you again. Sam kisses like the only thing in the world is what he’s hanging onto in front of him. To be the center of that kind of focus and intimacy is staggering. His tongue dances against yours, pulling whimpers from deep inside your chest, while Dean continues to work his fingers in and out of you, up to three now. 

Without understanding exactly how, you are on your back on the bed now, Sam climbing over you to bite at your neck and your breasts. The sting is delicious. 

“Sam,” you sigh breathlessly, his assault on your body sending shivers down between your legs. You glance around, looking for Dean, and find him across the room, rummaging through the bag Sam had gotten the rope out of earlier. The sight of his ass makes you groan, it’s always been one of your favorite parts to ogle. 

“So, how we doing this princess?” Dean calls, returning to the bed with a bottle of lube in his hand. 

“Dean, why do you keep that in with your interrogation stash?” Sam side-eyes Dean suspiciously with all the teasing, ‘what the fuck’ energy of a little brother.

“Shut up,” Dean shoots back, only sparing Sam a glance before raking his eyes over your body, laying breathless and wrecked on the bed before him. “Y/N,” the use of your name shocks through you and you hold Dean’s gaze this time. “What do you want?” 

“Both of you,” your voice comes out as a whisper, somehow still nervous to admit just what you want even after everything they’ve done to you tonight. 

“Where?” Sam prods, a smirk on his face. 

You have to take a steadying breath before you can answer what you really want. “I want you both inside me. One on each side.” 

“You want to suck one of us off, while the other one fucks that sweet cunt?” Dean’s growl is hungry and excited, but you shake your head. 

“I didn’t mean my mouth.” You hear their sharp intakes of breath and love how much that statement seems to affect them. Sam’s eyes are shining. 

“You gonna let one of us fuck you in the ass?” Sam’s words are nearly a growl and you nod weakly. “You care who?” You shake your head. 

Dean is on the bed now too, teasing his fingers over your legs, moving in tiny circles closer and closer between your thighs. “Please,” you whisper. 

“We playing rock, paper, scissors for her ass Sammy?” 

“You know I’m gonna win Dean, just give me the damn lube.” 

“Yeah, whatever,” Dean grumbles but he hands the lube over anyways. “Lay down baby girl, we got you.” Dean presses you into the bed, then pulls you onto your side, facing him. You lean forward, eyes begging him to kiss you, and he obliges happily. 

Sam crawls behind you, and you hear the clap of a lid being opened somewhere. A moment later something cold and slick brushes against the folds between your legs, making you gasp into Dean’s mouth. Sam’s fingers drag slowly backwards and stop just over the small rose between your ass cheeks. He holds his finger there, tracing small, wet circles over your entrance and it is driving you insane. 

“Oh, God, please Sam,” you pant, trying to push your ass back onto his hand. 

“My God, you are a slut,” Sam laughs. “I’ve never heard anyone beg for it this much, have you Dean?” 

“It’s cute, isn’t it Sammy?” Dean smiles, bringing his own hand down between your legs to join his brother’s. “Go on three?” Dean asks, eyes meeting Sam’s over your writhing body. In answer, Sam starts to count. 

“1, 2, 3.” On three Dean and Sam both press their fingers inside you, Dean’s in your pussy and Sam’s in your ass. A deep, uncontrollable moan erupts from you. 

“Yeah, you like that princess?” Dean smirks, and all you can do is nod helplessly, relishing in the jerking movements inside you. Sam and Dean keep their fingers pumping in and out, matching their strokes, and pressing their fingers together through your body, rubbing small, delicious circles on the thin walls separating them. They both add another finger, Sam pressing more lube in with his, aiding the slide of his wonderfully long digits. 

“So,” Sam bites at your ear as he works, “just how much of a cockslut are you? You let other guys do this to you before?” His words are harsh and seductive but you gather after a moment that he’s trying to figure out how much he needs to prep you, if you’ve ever been fucked up the ass before. 

“No, no one else,” you admit, rocking your body down into their hands. “Just, on my own. By myself.” 

“Shit,” Dean groans, loving the image that painted in his mind. “You sure you’re up for this? Take a look darlin’, any of the toys you have as big as us?” You look down to where Dean is grinding his dick against your stomach and swallow heavily. 

“No, you’re bigger,” you admit, surging up to kiss Dean more as Sam pushes a third finger into your ass. 

“And you still want us both?” Sam asks. You nod, pushing away from Dean to kiss Sam. He shoves his tongue between your lips and completely captivates you. “Such a fucking slut,” Sam breathes when he pulls his mouth of yours, eyes searching you face for any last sign of hesitation. You meet his gaze as steadily as you can. 

“Please,” you beg, “please fuck me, please.” 

“Well, since you said please,” Dean smirks and pulls his hand away, only to replace it instantly with his cock, the hard, blunt head pushing into your slick cunt in one shove. You cry out, the relief of finally being filled washing over you. 

You melt back into Sam’s chest as Dean begins to fuck into you, grabbing your thigh and bringing it up to wrap around his hips and press your heal into his ass. Sam brings his free hand up to your face to brush the hair out of your eyes, tucking it gently behind your ear. 

“That feel good baby?” He smiles as you nodded eagerly. “Wait until you feel me.” Sam pulls his fingers out and presses the head of his dick up against your asshole. Slowly, agonisingly slowly Sam presses his cock inside you. The stretch is more than anything you have ever felt and the feel of him on his own would have been intoxicating but you had something even better. Sam and Dean could feel each other inside you, pressing against the small barrier separating the holes they were fucking. 

In unison, they each slid out until only the tips of their cocks were still inside you, then pounded back in. The feeling of ecstasy this awoke in you could only be released as a scream, and you buried your head against Dean’s chest as you began to mewl and grind yourself onto their dicks. 

Taking this as their cue, Sam and Dean set up a relentless pace. Sam tugged on the rope around your wrists and pulled your arms up over your head, trapping you against him as he fucked you into his brother. Streams of noises started leaving your mouth without your permission, eliciting grins from Sam and Dean. 

“Ah, uh, god, mmmmm, ohgod, ah, ah, please, jesus, ahhh,” 

“Yeah, you like that?” Sam grunted in your ear. “You like being our little whore?” A muffled 'mmmm', is all you can manage. 

“I don’t think I’ve ever seen a prettier little slut, you Sammy?” Dean groaned. 

“No, she is definitely the prettiest Dean. Wonder why she wanted you,” Sam teased. 

“Probably because I know how to do this,” Dean shot back as his hand moved down between your legs to rub firm circles over your clit. After barely ten seconds of the extra attention, a molten wave a pleasure curled up your body from you toes, right between your legs. You pressed your hips into his hand, stretching out for the ecstasy that was hovering just out of reach. One harsh thrust from Dean’s cock and a bruising kiss from Sam and you were crashing. It felt like the floor had fallen out from beneath you and your body was doused in hot water. 

Then you were floating, whimpering between them as your body convulsed, cinching tight around their cocks as they ground into, hips jerking. Sam came first, fisting one hand in you hair and tangling the other in the rope still binding your wrists. You felt his release inside you, and it felt almost soothing. Dean pulled your face to his and kissed you, freezing against your lips, his mouth open and panting into yours as he screwed up his face and came in a strangled silence. 

The look on Dean’s face was so painfully beautiful, you had to kiss him again. You gave him gentle kisses, fairy kisses, small and sweet and soothing. Sam was brushing his fingers through your hair, doing some soothing of his own, and trying to bring his breathing down to par. 

Sam and Dean must have exchanged another silent agreement while you weren’t looking because they pulled out of you at exactly the same time, dragging a gasp out of you along with their bodies. Sam reached up and untied your hands, bringing your wrists to his mouth and kissing them gingerly. 

Dean rolled you off of your side and onto your back between them, so you could look up at their faces, eyes fixed on you. 

“I guess, I don’t really know what to say here,” Sam laughed awkwardly, mussing his fingers through his hair. 

“Oh you mean you don’t have a standing by-line to use after threesomes?” You tried to laugh but you haven’t caught enough breath back in your lungs yet. Dean chuckled and dropped a small kiss to your shoulder. 

“Well, you were our first,” Dean smiled, “despite previous offers.” 

“Well I’ll be,” you flutter your lashes and adopt and airy southern drawl. “You sure know how to make a girl feel special.” 

“From the sounds of it I thought we did alright,” Sam put in, wrapping his arm over your warm body and cuddling against your side, cocooning you between him and his brother. You sigh at the comforting feeling breezing over you, drowning your senses in a warmth and peace you had all been reaching for. When you smile, you hope to God they can’t see the tinge of sadness in your eyes. 

“I mean...I knew I was going to Hell before, but you guys made it totally worth it.”


End file.
